1.1: 96 percent / sodium hydride / dimethylformamide / 0 - 20 °C 2.1: anhydrous sodium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 2.2: 220 mg / sulfuric acid / H2O; diethyl ether / 6 h / 20 °C 3.1: pyridine / diethyl ether / 0 - 20 °C 4.1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C 5.1: 78 percent / active neutral alumina / diethyl ether / 12 h / 20 °C View Scheme

1.1: 96 percent / sodium hydride / dimethylformamide / 0 - 20 °C 2.1: anhydrous sodium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 2.2: 220 mg / sulfuric acid / H2O; diethyl ether / 6 h / 20 °C 3.1: pyridine / diethyl ether / 0 - 20 °C 4.1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C 5.1: 78 percent / active neutral alumina / diethyl ether / 12 h / 20 °C 6.1: p-toluenesulfonic acid / benzene / 12 h / 50 °C View Scheme

1: With 2-acetyloxy-1-propene; toluene-4-sulfonic acid 24 h; Heating; 2: With sodium tetrahydroborate in ethanol 1.5 h; Heating; Further stages.;

sodium hydride in N,N-dimethyl-formamide T=0 - 20°C;

1.1: 96 percent / sodium hydride / dimethylformamide / 0 - 20 °C 2.1: anhydrous sodium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 2.2: 220 mg / sulfuric acid / H2O; diethyl ether / 6 h / 20 °C 3.1: pyridine / diethyl ether / 0 - 20 °C 4.1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C View Scheme